The Patent Document 1 discloses that alicyclic alcohols represented by the following general formula (III) include one useful as a starting material for a flavor mixture. The Patent Document also discloses a method for producing the alicyclic alcohols represented by the following general formula (III), wherein, for example, 4-isopropyl-1-methylcyclohexyl methanol is produced by reducing an unsaturated alcohol produced from 1-isopropyl-4-methyl-1,3-cyclohexadiene and formaldehyde by using an acid catalyst. However, the above method has problems such that, since 1-isopropyl-4-methyl-1,3-cyclohexadiene which is the starting material in this method has a conjugated double bond, the compound is deteriorated in stability under the presence of an acid catalyst, and moreover, since it has plural reaction active sites, it has low selectivity of reaction in low yield.
In addition, 1-isopropyl-4-methyl-1,3-cyclohexadiene which is the starting material is not contained in a usual natural essential oil in a high concentration, and therefore, it is necessary to use a distillation column having a number of steps, or to isolate by distillation after increasing the content of the intended diene compounds by isomerization reaction, which causes a major problem in terms of supply and price.

In the above formula (III), R1 represents an alkyl group having 1-4 carbon atoms. R1 represents an alkyl group having 1-4 carbon atoms.
The Non-patent Document 1 discloses that 4-isopropyl-1-methylcyclohexane carboxylic acid is produced by carbonylating p-menthene-1 using BF3 as a catalyst, which, however, requires a carbon monoxide pressure of 100 atm or higher for the carbonylation reaction. The Non-patent Document 1 discloses that, for the purpose of identification, 4-isopropyl-1-methylcyclohexane carboxylic acid thus obtained is subjected to methyl esterification followed by reducing by LiAlH4 to obtain 4-isopropyl-1-methylcyclohexyl methanol. However, it does not disclose a detailed description of the method.
When a carboxylic acid is subjected to alkyl esterification, in general, it is reacted with an alcohol in the presence of an acid catalyst by removing water. In the case of a tertiary branched carboxylic acid such as 4-isopropyl-1-methylcyclohexane carboxylic acid, however, the rate of esterification reaction is slow and the yield is low. Therefore, it is not easy to carry out alkyl esterification in an efficient manner after obtaining 4-isopropyl-1-methylcyclohexane carboxylic acid according to the method disclosed in the Non-patent Document 1. Thus, it cannot be said that it is a suitable industrial manufacturing method for obtaining an intended 4-isopropyl-1-methylcyclohexyl methanol in high yield.
Whereas the method for carbonylation of a monoene compound under the presence of HF is publicly known by the Patent Document 2, and the method for producing an alcoholic compound by hydrogenation of an carbonyl compound is publicly known by the Patent Document 3, it had not been known to combine these processes of carbonylation and hydrogenation with the process for producing an alicyclic alcohol represented by the above general formula (III) which is useful as a starting material for a flavor mixture. In addition, it had not been known to produce the above-described alicyclic alcohol easily by using, as a starting material, natural essential oils which are beneficial in terms of supply and price such as limonene that is an easily-available natural product.